Halogen Or Unsaturation Patents (Class 562/574)
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Patent number: 4535167Abstract: Chiral N-protected, N-substituted .alpha.-amino acids are described. These compounds are prepared by condensation of an N-protected .alpha.-amino acid with an aldehyde followed by the selective reductive cleavage of an oxazolidinone intermediate.Type: GrantFiled: May 23, 1983Date of Patent: August 13, 1985Assignee: Merck & Co. Inc.Inventor: Roger M. Freidinger
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Patent number: 4508921Abstract: A process for preparing .alpha.-alkyl amino acids by enantioretentive .alpha.-alkylation of .alpha.-amino acids is described. The products are bioactive compounds including some useful as therapeutic agents.Type: GrantFiled: June 28, 1984Date of Patent: April 2, 1985Assignee: Merck & Co., Inc.Inventors: Joseph S. Amato, Leonard M. Weinstock, Sandor Karady
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Patent number: 4492799Abstract: Novel halo-4-alkenoic acid compounds which are useful intermediates for the synthesis of insecticides and miticides.Type: GrantFiled: July 2, 1979Date of Patent: January 8, 1985Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler
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Patent number: 4484003Abstract: .beta.-Chloroalanine is prepared by reacting in an aqueous medium an aziridine-2-carboxylate with hydrogen chloride in an amount of 2.0-5.0 moles per mole of the aziridine-2-carboxyalte and causing the thus-formed .beta.-chloroalanine to selectively crystallize out from the liquid reaction mixture. Since the solution recovered after the isolation of the crystallized .beta.-chloroalanine still contains .beta.-chloroalanine and by-produced .alpha.-chloro-.beta.-alanine dissolved therein, they may be converted into an aziridine-2-carboxylate by treating them with a base to recirculate it for reuse.Type: GrantFiled: December 29, 1982Date of Patent: November 20, 1984Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Masaharu Ohoka, Toshio Katoh, Ryuichi Mita, Nobuyuki Kawashima, Chojiro Higuchi, Nobuhiro Kawashima, Akihiro Yamaguchi, Shousuke Nagai, Takao Takano
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Patent number: 4454156Abstract: (R,S)- and (S)-4-amino-hepta-5,6-dienoic acid are novel inhibitors of gamma-aminobutyric acid transaminase (GABA-T).Type: GrantFiled: May 9, 1983Date of Patent: June 12, 1984Assignee: Merrell-Toraude et CompagnieInventor: Patrick Casara
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Patent number: 4436910Abstract: Aqueous solutions of sodium salts of .alpha.-aminocarboxylic acids practically free of foreign salts are produced by saponifying the corresponding hydantoin at a temperature between 110.degree. C. and 180.degree. C. with a mixture, in each case based on the hydantoin, of 1 equivalent of sodium hydroxide and 2 equivalents of calcium oxide or hydroxide, separating off the precipitated calcium carbonate after the end of the saponification and concentrating the aqueous sodium salt solution remaining to drive off the ammonia contained therein.Type: GrantFiled: February 10, 1982Date of Patent: March 13, 1984Assignee: Degussa AktiengesellschaftInventors: Axel Kleemann, Bernd Lehmann, Jurgen Martens
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Patent number: 4431817Abstract: Novel 1-fluoromethyl-substituted alkyl amines are disclosed. The novel compounds have biological activity including decarboxylase inhibition.Type: GrantFiled: April 14, 1980Date of Patent: February 14, 1984Assignee: Merck & Co., Inc.Inventors: Arthur A. Patchett, Janos Kollonitsch
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Patent number: 4418077Abstract: Fluorinated aminobutyric acid and diaminobutane compounds in vivo are inhibitors of gamma-aminobutyric acid transaminase and have the following formula: ##STR1## wherein: Y represents hydrogen or fluorine;Z represents --CH.sub.2 NR.sub.1 R.sub.2, where R.sub.1 and R.sub.2 are as defined below, or --COR.sub.3 where R.sub.3 is as defined below;R.sub.a represents hydrogen or R.sub.4, where R.sub.4 is as defined below;R.sub.1 represents hydrogen, C.sub.1 -C.sub.6 alkyl or phenyl-(C.sub.1 -C.sub.4 alkyl);R.sub.2 represents hydrogen, C.sub.1 -C.sub.6 alkyl, phenyl-(C.sub.1 -C.sub.4 alkyl) or, when R.sub.a is hydrogen, R.sub.4, where R.sub.4 is as defined below;R.sub.3 represents hydroxy, or when R.sub.a is hydrogen, C.sub.1 -C.sub.8 alkoxy, --NR.sub.5 R.sub.6, where R.sub.5 and R.sub.6 are as defined below, or an aminocarboxylic acid residue derived by removal of an hydrogen atom from the amino moiety of an L-aminocarboxylic acid;each R.sub.4, independently, represents C.sub.2 -C.sub.Type: GrantFiled: August 21, 1981Date of Patent: November 29, 1983Assignee: Merrell Toraude et CompagnieInventors: Philippe Bey, Fritz Gerhart, Michel Jung, Daniel Schirlin
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Patent number: 4386103Abstract: Dichloroamino acid derivatives other than .alpha.-dichloroamino acids are prepared from chlorination of corresponding amino acids, and are found to be potent germicidal and fungicidal agents.Type: GrantFiled: January 30, 1981Date of Patent: May 31, 1983Assignee: Merck & Co., Inc.Inventors: Stefano A. Pogany, Takeru Higuchi
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Patent number: 4351954Abstract: Halogenated .alpha.-amino acids as new compounds are obtained by subjecting halogenated ethanes and an ester of acrylic acid or crotonic acid to addition reaction, adding sodium azide to the adducts, reducing the resultant mixtures with hydrogen and subsequently hydrolyzing the reduction products.Type: GrantFiled: August 3, 1981Date of Patent: September 28, 1982Assignees: Agency of Industrial Science & Technology, Ministry of International Trade & IndustryInventors: Hiroshige Muramatsu, Teruo Ueda
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Patent number: 4326071Abstract: Novel compounds of the following general formula are useful pharmacological agents: ##STR1## wherein Y is FCH.sub.2 - or F.sub.2 CH-; R.sub.1 is hydroxy, a straight or branched alkoxy group of from 1 to 8 carbon atoms, -NR.sub.10 R.sub.11 wherein each of R.sub.10 and R.sub.11 is hydrogen or a straight or branched alkyl group of from 1 to 4 carbon atoms or ##STR2## wherein R.sub.12 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; R.sub.2 is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 4 carbon atoms and is straight or branched, alkoxycarbonyl wherein the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched or ##STR3## wherein R.sub.8 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; and n is the integer 2 or 3; pharmaceutically acceptable salts and individual optical isomers thereof.Type: GrantFiled: September 28, 1977Date of Patent: April 20, 1982Assignee: Merrell Toraude et CompagnieInventors: Philippe Bey, Michel Jung
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Patent number: 4301186Abstract: This invention relates to new ammonium salts of .alpha.-ketocarboxylic acids, to their use for the production of amines in situ by photochemical decomposition and to photochemically hardenable coating compositions containing these ammonium salts.Type: GrantFiled: June 28, 1979Date of Patent: November 17, 1981Assignee: Bayer AktiengesellschaftInventors: Wolfram Mayer, Hans Rudolph, Eckhard De Cleur, Manfred Schonfelder
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Patent number: 4283554Abstract: A novel production process of .beta.-chloroalanine from chloroacetaldehyde is provided. In this process, a bisulfite or sulfite addition compound of chloroacetaldehyde is first reacted, in an aqueous solution, with ammonia and, then, reacted with hydrocyanic acid or a salt thereof. Thus, .alpha.-amino-.beta.-chloropropionitrile is formed. This .alpha.-amino-.beta.-chloropropionitrile is hydrolyzed under an acidic condition to form .beta.-chloroalanine.Type: GrantFiled: May 29, 1980Date of Patent: August 11, 1981Assignee: Showa Denko Kabushiki KaishaInventors: Chozo Inoue, Soyao Moriguchi
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Patent number: 4264590Abstract: It has been found that dipeptides containing a 3-halo-D-alanine C-terminus are powerful antibacterials and produce a highly useful synergistic effect with antibiotics.Type: GrantFiled: June 9, 1980Date of Patent: April 28, 1981Assignee: Abbott LaboratoriesInventors: Daniel I. Chu, Jerry R. Martin, Alford M. Thomas, Norman E. Wideburg
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Patent number: 4254284Abstract: Novel compounds of the following general formula are useful in the preparation of 4-aminohex-5-enoic acid and 4-aminohex-5-ynoic acid which are useful pharmacological agents: ##STR1## wherein R.sub.1 is hydroxy, amino, or tert-butoxy.Type: GrantFiled: January 14, 1980Date of Patent: March 3, 1981Assignee: Merrell Toraude et CompagnieInventors: Maurice W. Gittos, Gerard J. Letertre
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Patent number: 4248677Abstract: This invention relates to a process for producing alpha-aminocarboxylic acids and salts thereof. More specifically, this invention relates to a process for producing alpha-aminocarboxylic acids or salts thereof from organic imine compounds by electrochemical reduction.Type: GrantFiled: July 10, 1979Date of Patent: February 3, 1981Assignee: Tokuyama Soda Kabushiki KaishaInventor: Shozo Kato
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Patent number: 4239916Abstract: New catalysts for isocyanurate foams are those comprising aminomethacrylate salts. The foams are obtained by the polymerization of an aromatic polyisocyanate, and a polyether or polyester polyol in the presence of a blowing agent and said amino methacrylate salts falling within the following structural formula: ##STR1## where the radicals represented by R are hydroxy lower alkyl, and M is selected from the group consisting of sodium, potassium, cesium, lithium and rubidium. The novel foams are useful in preparing rigid, flexible, semi-rigid, or semi-flexible materials such as panels, slabs or sprayed foam surfaces.Type: GrantFiled: October 30, 1978Date of Patent: December 16, 1980Assignee: Texaco Development Corp.Inventors: Robert L. Zimmerman, Edward E. McEntire, Howard P. Klein
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Patent number: 4228102Abstract: What is disclosed is a method for making amides of the formula ##STR1## wherein R.sub.1 is hydrogen or methyl,R.sub.3 is straight-chain or branched alkyl or unsubstituted or substituted aryl, andR.sub.4 is hydrogen or straight-chain or branched unsubstituted or substituted alkyl, which comprises reacting an ester of the formula ##STR2## wherein R.sub.2 is alkyl having 1 to 6 carbon atoms, with heating and under autogenous pressure, in a homogeneous phase, with an amine of the formula ##STR3## said amine being present in an amount which is stoichiometrically deficient up to an amount which is in small stoichiometric excess with respect to said ester.Type: GrantFiled: February 23, 1979Date of Patent: October 14, 1980Assignee: Rohm GmbHInventors: Siegmund Besecke, Wolfgang Gaenzler, Guenter Schroeder
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Patent number: 4219660Abstract: There are disclosed herein derivatives of bisfunctionalized compounds, wherein said compounds have been formed by the introduction of a nitro group and a hydroxyl group in the form of an ester into a conjugated diene molecule by treatment of said conjugated dienes with nitric acid in the presence of a carboxylic acid anhydride. The novel compounds produced by this process are useful as bactericides, fungicides and valuable organic synthesis intermediates.Type: GrantFiled: June 24, 1977Date of Patent: August 26, 1980Assignee: Hoffmann-La Roche Inc.Inventor: Pius A. Wehrli
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Patent number: 4178463Abstract: Novel compounds of the following general formula are useful in the preparation of 4-aminohex-5-enoic acid and 4-aminohex-5-ynoic acid which are useful pharmacological agents: ##STR1## wherein R.sub.1 is hydroxy, amino, or tert-butoxy.Type: GrantFiled: January 30, 1978Date of Patent: December 11, 1979Assignee: Merrell Toraude et CompagnieInventors: Maurice W. Gittos, Gerard J. Letertre
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Patent number: 4160777Abstract: Textiles, particularly carpets, are endowed with oil and water repellency and soil resistance by treatment thereof with certain detergent-compatible fluorochemmical compounds which can also be used in conjunction with anionic or nonionic detergents to provide cleaning/treating compositions for cleaning such textiles simultaneously with the treatment. The textile treating compositions of the invention comprise certain detergent-compatible fluorochemical compounds which are dissolved and/or dispersed in a suitable liquid vehicle. The textile treating/cleaning compositions of the invention also contain an anionic and/or a nonionic detergent.Type: GrantFiled: January 14, 1977Date of Patent: July 10, 1979Assignee: Minnesota Mining and Manufacturing CompanyInventor: Basil L. Loudas
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Patent number: 4149012Abstract: The racemate of 3-fluoro-alanine, and salts thereof, are prepared by reductive amination of 3-fluoro-pyruvic acid, its hydrate, or salts thereof, via the intermediate 2-imino-3-fluoro propionic acid salt, using alkali metal borohydrides as reducing agents. The racemates thus obtained are valuable in the production of 3-fluoro-D-alanine and its pharmacologically acceptable salts, and derivatives thereof, which are potent antibacterial agents.Type: GrantFiled: October 7, 1977Date of Patent: April 10, 1979Assignee: Merck & Co., Inc.Inventors: Ulf-H. Dolling, Edward J. J. Grabowski, Erwin F. Schoenewaldt, Meyer Sletzinger
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Patent number: RE31980Abstract: Novel compounds of the following general formula are useful pharmacologic agents: ##STR1## R is .[.selected from.]. hydrogen.[., alkylcarbonyl wherein the alkyl moiety contains from 1 to 4 carbon atoms, alkoxycarbonyl wherein the alkoxy moiety contains from 1 to 4 carbon atoms and may be straight or branched, and ##STR2## wherein R.sub.10 is selected from hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl and p-hydroxybenzyl.].; R.sub.2 is .[.selected from.]. hydroxy.[., a straight or branched alkoxy group of from 1 to 8 carbon atoms, a lower alkylamino group wherein the alkyl moiety contains from 1 to 4 carbon atoms, and ##STR3## wherein R.sub.4 is selected from hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl, and p-hydroxybenzyl.].; R.sub.3 is .[.selected from.]. hydrogen.[., chlorine, bromine, and iodine.].; [A] is .[.selected from.]. ##STR4## .[.and --CH.dbd.CH--.]. wherein R.sub.1 is .[.selected from.]. hydrogen.[.Type: GrantFiled: January 14, 1983Date of Patent: September 3, 1985Assignee: Merrell Toraude et CompagnieInventors: Brian W. Metcalf, Michel Jung